(2R,4S,5S)-5-Azido-2-benzhydryl-tetrahydropyran-4-ol → (2R,4S,5S)-5-amino-2-benzhydryl-tetrahydropyran-4-ol

HRID 1897926Notes

Reaction equation

HRID 1897926 reaction equation
[N:1]([C@H:4]1[CH2:9][O:8][C@@H:7]([CH:10]([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[CH2:6][C@@H:5]1[OH:23])=[N+]=[N-]>CO>[NH2:1][C@H:4]1[CH2:9][O:8][C@@H:7]([CH:10]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[CH2:6][C@@H:5]1[OH:23]

Participants

3

Reactant 1

HCID 11681112(2R,4S,5S)-5-Azido-2-benzhydryl-tetrahydropyran-4-ol

Product 1

HCID 11594377(2R,4S,5S)-5-amino-2-benzhydryl-tetrahydropyran-4-olYield 100.8%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

(2R,4S,5S)-5-Azido-2-benzhydryl-tetrahydropyran-4-ol (0.05 g, 0.14 mmol) was hydrogenated (Procedure G) to yield (2R,4S,5S)-5-amino-2-benzhydryl-tetrahydropyran-4-ol 0.04 g (97%, [α]D=(+) 66.2, c=1, MeOH).

Sources & evidence

ORD record
ord-827b555edfde46e1ba0fb6eb9dec59c2
Source dataset
uspto-grants-2013_08
Patent number
US08519159B2

Reaction notes

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